SYNTHESIS OF N-CHAIN AND SIDE-CHAIN PROTECTED ASPARTYL AND GLUTAMYL ALDEHYDE DERIVATIVES - REINVESTIGATION OF THE REDUCTION OF WEINREB AMIDES

Citation
M. Paris et al., SYNTHESIS OF N-CHAIN AND SIDE-CHAIN PROTECTED ASPARTYL AND GLUTAMYL ALDEHYDE DERIVATIVES - REINVESTIGATION OF THE REDUCTION OF WEINREB AMIDES, Tetrahedron letters, 39(11), 1998, pp. 1341-1344
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404039
Volume
39
Issue
11
Year of publication
1998
Pages
1341 - 1344
Database
ISI
SICI code
0040-4039(1998)39:11<1341:SONASP>2.0.ZU;2-4
Abstract
The reduction of Weinreb amides was reinvestigated in order to find co nditions that will allow the synthesis of protected aspartyl and gluta myl aldehydes derivatives useful for peptide and pseudopeptide synthes es. We have demonstrated that lithium tris(tert-butoxy)aluminium hydri de [LiAl(OtBu)(3)H] and lithium tris[(3-ethyl-3-pentyl)oxy]aluminium h ydride (LTEPA) can be used to reduce Weinreb amide derivatives into th eir corresponding aldehydes. In these conditions, it was possible to s ynthesize N- and side chain protected aspartyl and glutamyl aldehyde d erivatives in fairly good conditions. (C) 1998 Elsevier Science Ltd. A ll rights reserved.